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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:24:12 UTC
HMDB IDHMDB0000224
Secondary Accession Numbers
  • HMDB0012279
  • HMDB00224
  • HMDB0060151
  • HMDB0060152
  • HMDB12279
  • HMDB60151
  • HMDB60152
Metabolite Identification
Common NameO-Phosphoethanolamine
DescriptionO-Phosphoethanolamine, also known as PEA, phosphorylethanolamine, colamine phosphoric acid or ethanolamine O-phosphate, belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. O-Phosphoethanolamine is used in the biosynthesis of two different types of phospholipids: glycerophospholipids and sphingolipids. O-Phosphoethanolamine exists in all living species, ranging from bacteria to plants to humans. Within humans, O-phosphoethanolamine participates in a number of enzymatic reactions. In particular, cytidine triphosphate and O-phosphoethanolamine can be converted into CDP-ethanolamine; which is mediated by the enzyme ethanolamine-phosphate cytidylyltransferase. In addition, O-phosphoethanolamine can be biosynthesized from ethanolamine; which is catalyzed by the enzyme choline/ethanolamine kinase. In humans, O-phosphoethanolamine is involved in phosphatidylcholine biosynthesis. O-phosphoethanolamine is also a product of the metabolism of sphingolipids. In particular, sphinglipids are metabolized in vivo to phosphorylethanolamine and a fatty aldehyde, generally palmitaldehyde. Both metabolites are ultimately converted to glycerophospholipids. The lipids are first phosphorylated by a kinase and then cleaved by the pyridoxal-dependent sphinganine-1-phosphate aldolase. Elevated urine levels of O-Phosphoethanolamine or PEA can be used to help in the diagnosis of Hypophosphatasia (HPP). Reference ranges for urinary PEA vary according to age and somewhat by diet, and follow a circadian rhythm. Outside of the human body, O-phosphoethanolamine has been detected, but not quantified in, several different foods, such as oxheart cabbages, anises, shiitakes, abalones, and teffs.
Structure
Data?1582752117
Synonyms
ValueSource
2-Amino-ethanol dihydrogen phosphateChEBI
2-Amino-ethanol phosphateChEBI
Colamine phosphateChEBI
Colamine phosphoric acidChEBI
Colaminphosphoric acidChEBI
EAPChEBI
Ethanolamine acid phosphateChEBI
Ethanolamine O-phosphateChEBI
Ethanolamine phosphateChEBI
mono(2-Aminoethyl) phosphateChEBI
Monoaminoethyl phosphateChEBI
O-PhosphocolamineChEBI
O-PhosphorylethanolamineChEBI
OPEChEBI
PEChEBI
PEAChEBI
PETNChEBI
PhosphoethanolamineChEBI
PhosphonoethanolamineChEBI
Phosphoric acid 2-aminoethyl phenyl esterChEBI
Phosphoryl-ethanolamineChEBI
2-Amino-ethanol dihydrogen phosphoric acidGenerator
2-Amino-ethanol phosphoric acidGenerator
ColaminphosphateGenerator
Ethanolamine acid phosphoric acidGenerator
Ethanolamine O-phosphoric acidGenerator
Ethanolamine phosphoric acidGenerator
mono(2-Aminoethyl) phosphoric acidGenerator
Monoaminoethyl phosphoric acidGenerator
Phosphate 2-aminoethyl phenyl esterGenerator
2-Amino-ethanol dihydrogen phosphate (ester)HMDB
2-Aminoethanol O-phosphateHMDB
2-Aminoethyl dihydrogen phosphateHMDB
2-Aminoethyl dihydrogen phosphate (acd/name 4.0)HMDB
2-Aminoethyl phosphateHMDB
Colamine acid phosphateHMDB
Colaminephosphoric acidHMDB
EthampHMDB
O-PhosphonatoethanaminiumHMDB
PhosphoryethanolamineHMDB
PhosphorylethanolamineHMDB
Phosphorylethanolamine, 3H-labeled CPDHMDB
Phosphorylethanolamine magnesium (1:1) saltHMDB
Phosphorylethanolamine zinc saltHMDB
Phosphorylethanolamine, cobalt (2+) (1:1) saltHMDB
Calcium 2-aminoethanol phosphateHMDB
Phosphorylethanolamine ca (1:1) saltHMDB
Chemical FormulaC2H8NO4P
Average Molecular Weight141.063
Monoisotopic Molecular Weight141.019094261
IUPAC Name(2-aminoethoxy)phosphonic acid
Traditional Namephosphorylethanolamine
CAS Registry Number1071-23-4
SMILES
NCCOP(O)(O)=O
InChI Identifier
InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
InChI KeySUHOOTKUPISOBE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhosphoethanolamines
Alternative Parents
Substituents
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point241 - 243 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility72 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility25.8 g/LALOGPS
logP-1.5ALOGPS
logP-2.5ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)1.54ChemAxon
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.08 m³·mol⁻¹ChemAxon
Polarizability11.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0fki-0910000000-63541b89e6730018e48b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0h9a-1921000000-3a1d4ab89b928259f71d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-0910000000-63541b89e6730018e48b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-0911000000-7fc066f17e2ebf6c84f82017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9100000000-543d2d90aa663406e9992016-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-88dc3b66f275af50de342014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9100000000-993b8efd11624567ec4b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-f2fd3c258685af07afb52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b479823e7c0ee6b5e03d2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-2900000000-9cf72ee86018eb78504f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-169b03f94a9f53bd0de42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-199d7ab7a4aeb040674e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-f573b62dada3630598c32012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-38c04ce07a85a8db342c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9100000000-b582c6b51602884756da2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-2900000000-9cf72ee86018eb78504f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-169b03f94a9f53bd0de42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-199d7ab7a4aeb040674e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-f573b62dada3630598c32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-38c04ce07a85a8db342c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9100000000-b582c6b51602884756da2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-4335e927ba2537543f7d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-3e5f10c6e140e555b9fe2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9300000000-a9eb3cce3bf5c7453bd22015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4c92e75f13cc6c5119eb2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5874389316d6cd66936a2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-9800000000-b5c7c61b118c38407fa52015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-b562b8507dff78a49e4d2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfba6ec4cc15f40c63552015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-9cf36baccac69593c69f2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-9000000000-f40f44aa7120ad3f9c532021-09-06View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, D2O, experimental)2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified19 +/- 9.9 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified4.0 +/- 2.0 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified6.0 +/- 1.1 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified6.30 (4.70-9.60) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified50.9 +/- 34.1 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified66.2 +/- 20.4 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified76.2 +/- 64.8 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified14.8 +/- 17.4 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified30.53 +/- 32.79 umol/mmol creatinineNewborn (0-30 days old)Not Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified<9.95 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0-53 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified142.263 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified<5.43 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.69-38.57 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified3.73-38.69 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified4.276 (1.644-6.908) umol/mmol creatinineAdult (>18 years old)BothNormal
      Not Available
details
UrineDetected and Quantified2.15-18.55 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified8.2 +/- 2.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified<25 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.36-13.35 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified7.91 +/- 18.09 umol/mmol creatinineNewborn (0-30 days old)Not Specified
Normal
details
UrineDetected and Quantified10.18 +/- 12.44 umol/mmol creatinineNewborn (0-30 days old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified11.3 (6.50-16.4) uMAdult (>18 years old)Both
Brain injury
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
UrineDetected and Quantified71.48 +/- 35.869 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified84 umol/mmol creatinineChildren (1-13 years old)FemaleOdontohypophosphatasia details
Associated Disorders and Diseases
Disease References
Traumatic brain injury
  1. Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. [PubMed:15756940 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Odontohypophosphatasia
  1. Haliloglu B, Guran T, Atay Z, Abali S, Mornet E, Bereket A, Turan S: Infantile loss of teeth: odontohypophosphatasia or childhood hypophosphatasia. Eur J Pediatr. 2013 Jun;172(6):851-3. doi: 10.1007/s00431-012-1868-4. Epub 2012 Oct 24. [PubMed:23093139 ]
Associated OMIM IDs
DrugBank IDDB01738
Phenol Explorer Compound IDNot Available
FooDB IDFDB021911
KNApSAcK IDNot Available
Chemspider ID990
KEGG Compound IDC00346
BioCyc IDPHOSPHORYL-ETHANOLAMINE
BiGG ID1485304
Wikipedia LinkPhosphorylethanolamine
METLIN ID5233
PubChem Compound1015
PDB IDNot Available
ChEBI ID17553
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000106
References
Synthesis ReferenceMuller K; Schulz J; Oemus R Phosphoethanolamine--a substrate of alkaline phosphatase isolated from rat calvaria. Biomedica biochimica acta (1989), 48(8), 495-504.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  2. Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. [PubMed:15756940 ]
  3. Klunk WE, Debnath ML, McClure RJ, Pettegrew JW: Inactivity of phosphoethanolamine, an endogenous GABA analog decreased in Alzheimer's disease, at GABA binding sites. Life Sci. 1995;56(26):2377-83. [PubMed:7791524 ]
  4. Klunk WE, McClure RJ, Xu CJ, Pettegrew JW: Structural determinants of activity at the GABAB receptor. A comparison of phosphoethanolamine and related GABA analogs. Mol Chem Neuropathol. 1995 Sep;26(1):15-30. [PubMed:8588821 ]
  5. Li G, Foote C, Alexander S, Alexander H: Sphingosine-1-phosphate lyase has a central role in the development of Dictyostelium discoideum. Development. 2001 Sep;128(18):3473-83. [PubMed:11566853 ]
  6. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
Gene Name:
PCYT2
Uniprot ID:
Q99447
Molecular weight:
35199.52
Reactions
Cytidine triphosphate + O-Phosphoethanolamine → Pyrophosphate + CDP-ethanolaminedetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
Gene Name:
CHKB
Uniprot ID:
Q9Y259
Molecular weight:
45270.99
Reactions
Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.
Gene Name:
CHKA
Uniprot ID:
P35790
Molecular weight:
52248.53
Reactions
Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Highly specific for ethanolamine phosphorylation. May be a rate-controlling step in phosphatidylethanolamine biosynthesis.
Gene Name:
ETNK1
Uniprot ID:
Q9HBU6
Molecular weight:
27994.955
Reactions
Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine. Elevates stress-induced ceramide production and apoptosis.
Gene Name:
SGPL1
Uniprot ID:
O95470
Molecular weight:
63523.265
Reactions
Sphinganine 1-phosphate → O-Phosphoethanolamine + Palmitaldehydedetails
Sphingosine 1-phosphate → O-Phosphoethanolamine + Hexadecenaldetails
General function:
Involved in phosphatase activity
Specific function:
Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
Gene Name:
PHOSPHO1
Uniprot ID:
Q8TCT1
Molecular weight:
32350.505
Reactions
O-Phosphoethanolamine + Water → Ethanolamine + Phosphatedetails
General function:
Involved in transaminase activity
Specific function:
Catalyzes the pyridoxal-phosphate-dependent breakdown of phosphoethanolamine, converting it to ammonia, inorganic phosphate and acetaldehyde.
Gene Name:
AGXT2L1
Uniprot ID:
Q8TBG4
Molecular weight:
55039.64
Reactions
O-Phosphoethanolamine + Water → Acetaldehyde + Ammonia + Phosphatedetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Highly specific for ethanolamine phosphorylation. Does not have choline kinase activity (By similarity).
Gene Name:
ETNK2
Uniprot ID:
Q9NVF9
Molecular weight:
44781.125
Reactions
Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
General function:
Involved in catalytic activity
Specific function:
Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
Gene Name:
ENPP6
Uniprot ID:
Q6UWR7
Molecular weight:
50240.625
Reactions
1-(1-Alkenyl)-sn-glycero-3-phosphoethanolamine + Water → 1-(1-Alkenyl)-sn-glycerol + O-Phosphoethanolaminedetails
General function:
Not Available
Specific function:
Exhibits PLA1/2 activity, catalyzing the calcium-independent hydrolysis of acyl groups in various phosphotidylcholines (PC) and phosphatidylethanolamine (PE). For most substrates, PLA1 activity is much higher than PLA2 activity. Catalyzes N-acylation of PE using both sn-1 and sn-2 palmitoyl groups of PC as acyl donor. Also catalyzes O-acylation converting lyso-PC into PC.
Gene Name:
HRASLS2
Uniprot ID:
Q9NWW9
Molecular weight:
17393.695
Reactions
Phosphatidylcholine + O-Phosphoethanolamine → 1-acylglycerophosphocholine + N-palmitoyl-phosphoethanolaminedetails